22 days in Florida Itinerary

22 days in Florida Itinerary

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Route & dates

22 days in Florida Itinerary

Start: Edmonton
Fly:  13​h 30​min
1
Key West
— 3 nights
bus:  45​min
2
Big Pine Key
— 2 nights
Drive:  30​min
3
Marathon
— 3 nights
Drive:  1​h 30​min
4
Key Largo
— 2 nights
Drive:  1​h 30​min
5
Miami Beach
— 3 nights
Fly + Drive:  4​h 45​min
6
St. Augustine
— 3 nights
Drive:  2​h
7
Orlando
— 4 nights
Fly:  9​h 45​min
End: Edmonton

3
nights
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Do your shopping at Alan S. Maltz Gallery and 7 Artists & Friends. There's much more to do: examine the collection at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, take a leisurely stroll along Mallory Square, and hunt for treasures at Sunset Celebration.

To find other places to visit, maps, more things to do, and more tourist information, use the Key West driving holiday website .

Edmonton, Canada to Key West is an approximately 13.5-hour flight. You can also do a combination of bus and flight; or drive. The time zone changes from Mountain Standard Time (MST) to Eastern Standard Time (EST), which is usually a 2 hour difference. When traveling from Edmonton in May, plan for somewhat warmer days in Key West, with highs around 34°C, while nights are warmer with lows around 29°C. Wrap up your sightseeing on the 17th (Fri) early enough to take a bus to Big Pine Key.

Things to do in Key West

Museums Historic Sites Parks
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery

2
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 18th (Sat), stop by Out of the Blue Gallery, then enjoy the sand and surf at Calusa Beach, and then immerse yourself in nature at Bahia Honda State Park. On your second day here, look for all kinds of wild species at National Key Deer Refuge, take in the exciting artwork at Artists in Paradise Gallery, and then find your balance on the water with some of the best stand-up paddleboarding in the area.

To see ratings, photos, and tourist information, read Big Pine Key tour itinerary maker tool .

You can take a bus from Key West to Big Pine Key in an hour. Alternatively, you can drive. Expect a daytime high around 36°C in May, and nighttime lows around 29°C. Finish your sightseeing early on the 19th (Sun) to allow enough time to take a bus to Marathon.

Things to do in Big Pine Key

Outdoors Parks Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Artists in Paradise Gallery ©
Artists in Paradise Gallery

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Your itinerary includes some good beach time at Sombrero Beach and Sunset Park Beach. Shop till you drop at Christina's Consignment Boutique and Michelle Nicole Lowe Art Gallery. Take a break from Marathon with a short trip to Florida Keys Brewing Company in Islamorada, about 38 minutes away. There's much more to do: get all the information you need at Pigeon Key Foundation, soothe aching muscles at some of the top local wellness centers, take in the architecture and atmosphere at San Pablo Catholic Church, and identify plant and animal life at Crane Point Museum & Nature Center.

For reviews, photos, maps, and more tourist information, you can read our Marathon trip itinerary planning tool .

Marathon is very close to Big Pine Key. In May in Marathon, expect temperatures between 36°C during the day and 29°C at night. Finish your sightseeing early on the 22nd (Wed) so you can drive to Key Largo.

Things to do in Marathon

Parks Beaches Outdoors

Side Trips

Islamorada, Sunset Park Beach
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Sunset Park Beach ©
Sunset Park Beach
Pigeon Key Foundation ©
Pigeon Key Foundation

2
nights
Key Largo

Key Largo ©
The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Start off your visit on the 23rd (Thu): look for gifts at Shell World Florida Keys, then meet the residents at Island Dolphin Care, and then see some colorful creatures with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, view the masterpieces at Lobster Trap Art Gallery, indulge your thirst for a good beer at Islamorada Beer Company Brewery and Tasting Room, then cast your line with a fishing tour, and finally get some fabulous bargains at Sandal Factory Outlet.

To see ratings, where to stay, and other tourist information, you can read our Key Largo vacation planner .

You can drive from Marathon to Key Largo in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Traveling from Marathon in May, expect little chillier with lows of 26°C in Key Largo. Finish up your sightseeing early on the 24th (Fri) so you can go by car to Miami Beach.

Things to do in Key Largo

Wildlife Outdoors Tours

Side Trip

Islamorada
Highlights from your plan
Lobster Trap Art Gift Shop and Gallery ©
Sandal Factory Outlet ©
Sandal Factory Outlet

3
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Head to Lincoln Road and Collins Avenuefor plenty of shopping. Explore Miami Beach's surroundings by going to Aventura Mall (in Aventura), Dolphin Mall (in Miami) and Coral Gables (Village of Merrick Park & Lowe Art Museum). There's still lots to do: enjoy the sand and surf at South Beach, don't miss a visit to Bayside Marketplace, shop like a local with Britto Central, and appreciate the extensive heritage of Art Deco Historic District.

For traveler tips, other places to visit, reviews, and more tourist information, you can read our Miami Beach planning site .

You can drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Miami Beach can reach 36°C, while at night they dip to 27°C. Finish up your sightseeing early on the 27th (Mon) so you can travel to St. Augustine.

Things to do in Miami Beach

Shopping Neighborhoods Historic Sites

Side Trips

Miami, Coral Gables, Aventura Mall
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Aventura Mall ©
Aventura Mall

3
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Head to The Gifted Cork and Metalartz Galleryfor some retail therapy. We've included these beaches for you: St. Augustine Beach and Vilano Beach. Go for a jaunt from St. Augustine to Crescent Beach to see Crescent Beach Public Beach about 40 minutes away. And it doesn't end there: sample the fine beverages at St. Augustine Distillery, examine the collection at The Ximenez-Fatio House, identify plant and animal life at St. Augustine Wild Reserve, and browse the exhibits of St. Augustine Lighthouse & Maritime Museum, Inc..

To find maps, reviews, other places to visit, and other tourist information, you can read our St. Augustine road trip planning app .

You can do a combination of flight and car from Miami Beach to St. Augustine in 5 hours. Alternatively, you can drive; or take a bus. Expect slightly colder evenings in St. Augustine when traveling from Miami Beach in May, with lows around 22°C. Cap off your sightseeing on the 30th (Thu) early enough to go by car to Orlando.

Things to do in St. Augustine

Parks Beaches Outdoors

Side Trip

Crescent Beach Public Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Vilano Beach ©
Vilano Beach

4
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Pack the 31st (Fri) with family-friendly diversions at Discovery Cove. Have a day of magic on the 1st (Sat) at Walt Disney World Resort. And it doesn't end there: find something for the whole family at Universal Orlando Resort, buy something for everyone on your list at The Mall at Millenia, and discover the magic at Happily Ever After Fireworks.

To find photos, maps, more things to do, and other tourist information, refer to the Orlando attractions planner.

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. In May, daily temperatures in Orlando can reach 36°C, while at night they dip to 24°C. On the 3rd (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Orlando

Theme Parks Beaches Outdoors
Highlights from your plan
Discovery Cove ©
Discovery Cove
The Mall at Millenia ©
The Mall at Millenia
Walt Disney World Resort ©
Walt Disney World Resort

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